13 Of The Most Welcoming Towns In Vermont
Vermont, a state defined by its rolling green mountains and picturesque valleys, is as warm in spirit as it is beautiful in landscape. With small towns dotted across its winding roads, it is easy to stumble upon communities where friendliness is a way of life. From lively annual festivals to weekly farmers’ markets that feel like neighborhood reunions, these towns open their arms to locals and visitors alike. Whether you are joining a maple festival, a holiday parade, or a summer concert on the green, the people of Vermont know how to make everyone feel at home. Discover 13 of the most welcoming towns across the Green Mountain State.
Woodstock
Woodstock is a community that thrives on togetherness, offering year-round events that bring residents and visitors closer. The Woodstock Apples and Crafts Fair, held every October, fills the village green with local artisans, cheerful conversations, and autumn spirit. Winter is equally magical during the Wassail Weekend, a holiday festival featuring horse-drawn sleigh rides, caroling, and historic home tours.
Locals often say these events are what make Woodstock feel like a big family gathering rather than a small-town celebration. Even beyond its festivals, Woodstock’s community-driven atmosphere shows in the volunteers who organize concerts, charity events, and seasonal fairs.
Stowe
Stowe’s breathtaking mountain views are only part of its charm; the true magic lies in the warmth of its people. Every fall, the Stowe Foliage Arts Festival draws visitors from across New England for three days of music, art, and friendly conversation. Another beloved event, the British Invasion Car Show, turns Main Street into a festival of color and camaraderie, showcasing classic cars and shared enthusiasm.
Throughout the year, the Stowe Farmers Market serves as the town’s gathering place, where residents chat with travelers over coffee and handmade goods. Whether during ski season or summer, Stowe maintains a sense of hospitality that transcends tourism.
Brattleboro
Brattleboro is one of Vermont’s most eclectic and open-minded towns, known for its creativity and close-knit spirit. The Strolling of the Heifers Parade, celebrating local farms and food producers, perfectly reflects its community values and love of laughter. Locals also cherish the Brattleboro Literary Festival, which attracts authors and readers from across New England, turning the downtown into a hub of conversation and cultural exchange.
Events like the Gallery Walk and the gatherings at River Garden Marketplace reinforce Brattleboro’s reputation as a place where everyone is welcome.
Middlebury
Middlebury balances collegiate vibrancy with heartfelt small-town warmth. Each summer, locals and visitors gather on the town green for the Festival on the Green, a weeklong event featuring live music, family games, and regional food vendors. During the colder months, the Middlebury WinterFest keeps spirits high with ice carving, performances, and community bonfires that attract families from nearby towns.
The presence of Middlebury College strengthens the community’s welcoming nature, with students and residents frequently collaborating on volunteer projects and local events. The town’s open and inclusive character makes every gathering feel familiar, even to first-time visitors.
Manchester
Manchester’s reputation as a warm and sociable town is reflected in its year-round calendar of community events. The Manchester Fall Art and Craft Festival invites artisans from all over New England, transforming the town green into a lively hub of creativity and conversation. Each winter, residents gather for the Holiday Craft Fair, an event that doubles as a fundraiser for local charities.
Music lovers look forward to the Manchester Music Festival, a highlight of the summer season that draws audiences from near and far. The community’s enthusiasm for participation and volunteerism keeps every event vibrant and welcoming.
Waitsfield
Set in the scenic Mad River Valley, Waitsfield is a haven for those seeking friendship and community connection. The Waitsfield Farmers Market brings locals and visitors together each week, filled with live music, baked goods, and laughter. In summer, the Mad River Valley Craft Fair celebrates the area’s creativity, featuring artists and performers from across the region.
Events at the Round Barn Farm often anchor community life, from weddings to fundraisers, creating opportunities for both residents and travelers to mingle. Waitsfield’s openhearted culture makes everyone feel part of its close-knit circle.
Bennington
A strong sense of pride and belonging strengthens Bennington’s small-town charm. Every September, the Southern Vermont Garlic and Herb Festival draws thousands of visitors with its quirky mix of food, crafts, and music. In May, the Mayfest Arts and Crafts Festival transforms downtown into a street fair buzzing with activity and friendliness.
The town’s long-standing Bennington Battle Day Parade, honoring local Revolutionary War heroes, is a testament to community spirit that spans generations.
Montpelier
Montpelier may be the smallest capital city in the United States, but its heart is enormous. Community-led organizations like Montpelier Alive keep the town bustling with events such as the July 3rd Celebration, which features parades, live music, and fireworks. Another favorite is the Art Walk, where local artists showcase their work throughout downtown, creating a festive, inclusive atmosphere.
At the Capital City Farmers Market, residents greet visitors by name, exchanging more smiles than sales. Montpelier’s charm lies in its genuine openness, whether it’s a poetry reading or a civic gathering.
Shelburne
Shelburne’s sense of belonging is palpable from the moment you arrive. The Shelburne Day Celebration, held each August, brings residents and visitors together on the village green for music, local food, and community games. The Shelburne Harvest Festival at the Shelburne Vineyard is another local favorite, featuring hayrides, crafts, and agricultural demonstrations that honor Vermont’s farming heritage.
Throughout the year, the Shelburne Farmers Market serves as a meeting ground for neighbors and newcomers alike, where conversations flow easily between locals and travelers. Each event highlights the generosity and togetherness that define Shelburne’s culture.
Randolph
Randolph is a town where participation is a way of life. The Tunbridge World’s Fair, one of Vermont’s oldest traditions, attracts thousands with agricultural displays, live music, and old-fashioned games. In summer, the Make Music Day fills downtown with dancing and laughter, reinforcing the town’s welcoming nature.
Randolph’s Chandler Center for the Arts anchors much of the city's cultural life, regularly hosting performances that bring people from all over the state together. Events like the Vermont Pride Festival highlight the town’s inclusivity and celebration of diversity. Every gathering, big or small, reflects Randolph’s commitment to community engagement and warmth.
Bristol
Bristol is renowned for its lively festivals and genuine friendliness. The Bristol Fourth of July Celebration stands as one of Vermont’s most anticipated events, featuring an old-fashioned parade, fireworks, and family games. Each fall, the Bristol Harvest Festival transforms the town green into a bustling fairground filled with live performances, craft vendors, and shared laughter.
Community involvement is central to Bristol’s identity. Residents work tirelessly to organize events, fundraisers, and school fairs that benefit everyone.
Vergennes
Though Vermont’s smallest city, Vergennes, radiates friendliness on a grand scale. The Vergennes Day Festival is the highlight of summer, filling the city green with parades, music, and contests that draw visitors from miles around. Locals also take pride in the Vergennes Day Race, a spirited community run that celebrates health and togetherness. 2025 was its 44th year, and it includes a Kids 1K Fun Run, 5K Walk, and 5K, 10K, or 15K Run options.
Throughout the year, smaller gatherings, such as neighborhood concerts and community dinners, keep residents connected.
Ludlow
Ludlow’s charm lies in its ability to make visitors feel instantly at home. The Ludlow Farmers Market is a beloved gathering spot where locals exchange stories over handmade crafts and baked goods. Summer brings the Best of Vermont Summer Festival in Ludlow, which fills the streets with art, live music, and regional foods. Winter transforms the town with the Okemo Ski Resort LET IT GLOW Winter Ice Festival, featuring torchlight parades, family competitions, and community dinners.
The sense of unity in Ludlow is deeply rooted in volunteerism, with residents working together to keep events thriving.
Finding Your Community in Vermont
Vermont’s towns exemplify the warmth and sincerity that make small-town life so special. Each community, from Woodstock to Ludlow, cherishes its local traditions while eagerly welcoming newcomers. Whether it’s a festival, a fair, or a weekly market, these gatherings reveal what truly defines Vermont: genuine kindness, shared joy, and a deep sense of connection. Visitors often find that it isn’t just the landscapes that make Vermont memorable, but the people who fill them with laughter and care. These welcoming towns are a reminder that hospitality is timeless, and that in Vermont, community isn’t something you visit, it’s something you are invited into.
